Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H41N7O12.2ClH |
| Molecular Weight | 656.512 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 15 / 15 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.[H][C@@]2(O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC)[C@@H](O[C@@]3([H])[C@H](O)[C@@H](O)[C@H](NC(N)=N)[C@@H](O)[C@@H]3NC(N)=N)O[C@H](C)[C@@]2(O)CO
InChI
InChIKey=IONSYBIUIGVTJV-JOMTZEKMSA-N
InChI=1S/C21H41N7O12.2ClH/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35;;/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28);2*1H/t5-,6-,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,21+;;/m1../s1
DescriptionCurator's Comment: Description was created based on several sources, including
http://link.springer.com/chapter/10.1007%2F978-3-642-46304-4_36 | https://www.ncbi.nlm.nih.gov/pubmed/4133236 | https://www.ncbi.nlm.nih.gov/pubmed/27280286 |
https://www.ncbi.nlm.nih.gov/pubmed/13186082 | https://www.ncbi.nlm.nih.gov/pubmed/14925346 | https://www.ncbi.nlm.nih.gov/pubmed/13459234 | https://www.drugs.com/international/dihydrostreptomycin.html
Curator's Comment: Description was created based on several sources, including
http://link.springer.com/chapter/10.1007%2F978-3-642-46304-4_36 | https://www.ncbi.nlm.nih.gov/pubmed/4133236 | https://www.ncbi.nlm.nih.gov/pubmed/27280286 |
https://www.ncbi.nlm.nih.gov/pubmed/13186082 | https://www.ncbi.nlm.nih.gov/pubmed/14925346 | https://www.ncbi.nlm.nih.gov/pubmed/13459234 | https://www.drugs.com/international/dihydrostreptomycin.html
Dihydrostreptomycin is an antibiotic compound derived from streptomycin by reduction with hydrogen. The primary mechanism of action of the antibiotic dihydrostreptomycin is binding to and modifying the function of the bacterial ribosome, thus leading to decreased and aberrant translation of proteins, in addition it binds mechanosensitive channel of large conductance (MscL) and modifies its conformation, thus allowing the passage of K+ and glutamate out of, and dihydrostreptomycin into, the cell. It has about the same degree of antibacterial activity as streptomycin, but it is less effective against some gram-negative microorganisms. Because it has a higher risk of irreversible deafness, and its effectiveness is no greater that that of streptomycin, dihydrostreptomycin is no longer used clinically. To date dihydrostreptomycin is approved for veterinary use to treat bacterial infections.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14925346 | https://www.ncbi.nlm.nih.gov/pubmed/13459234
Curator's Comment: Dihydrostreptomycin is oto- and neurotoxic.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363135 |
94.0 nM [Kd] | ||
Target ID: P0A742 Gene ID: 947787.0 Gene Symbol: mscL Target Organism: Escherichia coli (strain K12) |
9.81 mM [Kd] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Unknown Approved UseUnknown |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1 g 1 times / day multiple, oral Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 21-64 years n = 3 Health Status: unhealthy Age Group: 21-64 years Sex: M+F Population Size: 3 Sources: |
Disc. AE: Hearing loss... AEs leading to discontinuation/dose reduction: Hearing loss (severe, 3 patients) Sources: |
2 g 1 times / day multiple, oral Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 29 years n = 1 Health Status: unhealthy Age Group: 29 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hearing loss... AEs leading to discontinuation/dose reduction: Hearing loss (severe, 1 patient) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Hearing loss | severe, 3 patients Disc. AE |
1 g 1 times / day multiple, oral Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 21-64 years n = 3 Health Status: unhealthy Age Group: 21-64 years Sex: M+F Population Size: 3 Sources: |
| Hearing loss | severe, 1 patient Disc. AE |
2 g 1 times / day multiple, oral Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 29 years n = 1 Health Status: unhealthy Age Group: 29 years Sex: F Population Size: 1 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. | 1993 Sep 24 |
|
| Antimicrobial resistance in Salmonella isolates from apparently healthy food-producing animal from 2000 to 2003: the first stage of Japanese veterinary antimicrobial resistance monitoring (JVARM). | 2006 Aug |
|
| Role of coresistance in the development of resistance to chloramphenicol in Escherichia coli isolated from sick cattle and pigs. | 2006 Feb |
|
| Development of a novel method based on liquid chromatography-evaporative light scattering detection for the direct determination of streptomycin and dihydrostreptomycin in raw materials, pharmaceutical formulations, culture media and plasma. | 2006 Jul 28 |
|
| Prioritizing genomic drug targets in pathogens: application to Mycobacterium tuberculosis. | 2006 Jun 9 |
|
| Depolarization of cochlear outer hair cells evokes active hair bundle motion by two mechanisms. | 2006 Mar 8 |
|
| [Present situation of national surveillance of antimicrobial resistance in bacteria isolated from farm animals in Japan and correspondence to the issue]. | 2006 May |
|
| A comparative randomized field trial on intramammary and intramuscular dry cow antibiotic treatment of subclinical Staphylococcus aureus mastitis in dairy cows. | 2006 Oct |
|
| Liquid chromatography on an amide stationary phase with post-column derivatization and fluorimetric detection for the determination of streptomycin and dihydrostreptomycin in foods. | 2007 Apr 30 |
|
| Quantitative determination of dihydrostreptomycin in bovine tissues and milk by liquid chromatography-electrospray ionization-tandem mass spectrometry. | 2007 May |
|
| Characterization of Klebsiella pneumoniae isolates from New Zealand sea lion (Phocarctos hookeri) pups during and after the epidemics on Enderby Island, Auckland Islands. | 2007 May 16 |
|
| Changes of multi-drug resistance pattern in Salmonella enterica subspecies enterica serovar typhimurium isolates from food-producing animals in Japan. | 2007 Nov |
|
| A high-throughput analytical method for determination of aminoglycosides in veal tissues by liquid chromatography/tandem mass spectrometry with automated cleanup. | 2007 Sep-Oct |
|
| Susceptibility of bacterial pathogens against lincomycin/spectinomycin (1/2), penicillin G/neomycin (1/1), and penicillin G/dihydrostreptomycin (1/1) as determined in the BfT-GermVet monitoring program 2004-2006. | 2007 Sep-Oct |
|
| The actions of calcium on hair bundle mechanics in mammalian cochlear hair cells. | 2008 Apr 1 |
|
| Multi-residue quantitation of aminoglycoside antibiotics in kidney and meat by liquid chromatography with tandem mass spectrometry. | 2008 Dec |
|
| Reaching activity in parietal area V6A of macaque: eye influence on arm activity or retinocentric coding of reaching movements? | 2008 Feb |
|
| Identification of genetic and chemical modulators of zebrafish mechanosensory hair cell death. | 2008 Feb 29 |
|
| Sperm morphology and chromatin integrity in Swedish warmblood stallions and their relationship to pregnancy rates. | 2008 Jan 7 |
|
| Clinical effects of transcatheter hepatic arterial embolization with holmium-166 poly(L-lactic acid) microspheres in healthy pigs. | 2008 Jul |
|
| [Simultaneous determination of aminoglycoside antibiotics in milk by liquid chromatography with tandem mass spectrometry]. | 2008 Jun |
|
| [Simple and rapid microbiological method for determination of residual antibacterials in meat]. | 2008 Jun |
|
| Monitoring of streptomycin and dihydrostreptomycin residual levels in porcine meat press juice and muscle via solid-phase fluorescence immunoassay and confirmatory analysis by liquid chromatography after post-column derivatization. | 2008 Mar |
|
| Phage type and antimicrobial susceptibility of Salmonella enterica serovar Enteritidis from food-producing animals in Japan between 1976 and 2004. | 2008 Oct |
|
| Farm-level impact of therapeutic antimicrobial use on antimicrobial-resistant populations of Escherichia coli isolates from pigs. | 2008 Sep |
|
| Toxin detection by surface plasmon resonance. | 2009 |
|
| Dihydrostreptomycin goes through the mechano-electric transduction channel in chick cochlear hair cells. | 2009 |
|
| Occurrence of antimicrobial residues in pasteurized milk commercialized in the state of Paraná, Brazil. | 2009 Apr |
|
| Treatment of mastitis during lactation. | 2009 Apr 1 |
|
| National surveillance of Salmonella enterica in food-producing animals in Japan. | 2009 Aug 25 |
|
| The chlamydial functional homolog of KsgA confers kasugamycin sensitivity to Chlamydia trachomatis and impacts bacterial fitness. | 2009 Dec 31 |
|
| Ascending cholangitis presenting with Lactococcus lactis cremoris bacteraemia: a case report. | 2009 Jan 6 |
|
| Changing prevalence of O-serogroups and antimicrobial susceptibility among STEC strains isolated from healthy dairy cows over a decade in Japan between 1998 and 2007. | 2009 Mar |
|
| Analysis of impurities in streptomycin and dihydrostreptomycin by hydrophilic interaction chromatography/electrospray ionization quadrupole ion trap/time-of-flight mass spectrometry. | 2009 Mar |
|
| Relationships between multidrug-resistant Salmonella enterica Serovar Schwarzengrund and both broiler chickens and retail chicken meats in Japan. | 2009 May |
|
| Phenotypic characterization of Salmonella typhimurium isolates from food-animals and abattoir drains in Buea, Cameroon. | 2009 Oct |
|
| Development and validation of an LC-APCI-MS-MS analytical method for the determination of streptomycin and dihydrostreptomycin residues in milk. | 2009 Oct |
|
| Microbial screening methods for detection of antibiotic residues in slaughter animals. | 2009 Oct |
|
| Defining features of the hair cell mechanoelectrical transducer channel. | 2009 Oct |
|
| Giardiavirus internal ribosome entry site has an apparently unique mechanism of initiating translation. | 2009 Oct 14 |
|
| Antimicrobial resistance and genetic characterization of fluoroquinolone-resistant Mannheimia haemolytica isolates from cattle with bovine pneumonia. | 2009 Oct 20 |
|
| An atypical case of respiratory actinobacillosis in a cow. | 2009 Sep |
|
| Stallion Sperm Viability, as Measured by the Nucleocounter SP-100, Is Affected by Extender and Enhanced by Single Layer Centrifugation. | 2010 |
|
| Recovery of mechano-electrical transduction in rat cochlear hair bundles after postnatal destruction of the stereociliar cross-links. | 2010 Aug 7 |
|
| Reproductive performance, udder health, and antibiotic resistance in mastitis bacteria isolated from Norwegian Red cows in conventional and organic farming. | 2010 Feb 8 |
|
| Monoclonal antibody-based ELISA and colloidal gold-based immunochromatographic assay for streptomycin residue detection in milk and swine urine. | 2010 Jan |
|
| Staphylococcus aureus sigma B-dependent emergence of small-colony variants and biofilm production following exposure to Pseudomonas aeruginosa 4-hydroxy-2-heptylquinoline-N-oxide. | 2010 Jan 30 |
|
| WD-repeat instability and diversification of the Podospora anserina hnwd non-self recognition gene family. | 2010 May 6 |
|
| Nano-vectors for the Ocular Delivery of Nucleic Acid-based Therapeutics. | 2010 Nov |
|
| CLIMP-63 is a gentamicin-binding protein that is involved in drug-induced cytotoxicity. | 2010 Nov 18 |
Patents
Sample Use Guides
Treatment of leptospirosis in dogs, horses and swine: 5 mg per pound of body weight.
Dihydrostreptomycin is used for intramammary use to reduce the frequency of existing infection and to prevent new infections with Staphylococcus aureus in dry cows.
Route of Administration:
Other
minimal inhibiting concentrations (MIC) of pure dihydrostreptomycin trihydrochloride against Mycobacterium smegmatis, Aerobacter aerogenes, Bacillus subtilis, Klebsiella pneumoniae, Serratia marcescens, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Mycobacterium tuberculosis, and Bacillus sp. range from 0.036 to 5.66 ug/ml depending on species
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F08EJ7FH4R
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884483-17-4
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72941937
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DTXSID30221988
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7177-56-2
Created by
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NON-SPECIFIC STOICHIOMETRY |
ACTIVE MOIETY
SUBSTANCE RECORD
